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Salicylic acid compounds with insulin-sensitizing activity and preparation method thereof

A kind of compound and acid technology, applied in the field of salicylic acid compound and preparation thereof

Inactive Publication Date: 2010-06-16
上海慈瑞医药科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no similar product with complete independent innovation and independent intellectual property rights entering the market in our country.

Method used

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  • Salicylic acid compounds with insulin-sensitizing activity and preparation method thereof
  • Salicylic acid compounds with insulin-sensitizing activity and preparation method thereof
  • Salicylic acid compounds with insulin-sensitizing activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: Synthesis of 2-acetoxy-4-n-butoxybenzoic acid (compound 1)

[0083] Step 1: Suspend 5 g of 2,4-dihydroxybenzoic acid in a mixture of acetic anhydride and acetic acid, add mixed acid [98% sulfuric acid: 37% hydrochloric acid=1:1] (V:V), seal and heat up Reaction at 85°C for 0.5h, hot suction filtration, the filtrate was cooled in an ice bath to precipitate solids, filtered, and the filter residue was dried under reduced pressure at 55°C;

[0084] Add anhydrous potassium carbonate and dry N,N-dimethylformamide to the above filter residue, add benzyl bromide dropwise, react at room temperature for 2 hours, filter, add ethyl acetate to the filtrate, wash with water and saturated brine in sequence, and wash the organic layer with Dry over sodium sulfate, use petroleum ether: ethyl acetate = 3:1 (V:V) as eluent, separate by silica gel column chromatography and evaporate to dryness to obtain intermediate (II);

[0085] Wherein, the mass ratio of 2,4-dihydroxybenzoi...

Embodiment 2

[0091] Embodiment 2: the synthesis of methyl 2-acetoxy-4-n-butoxybenzoate (compound 2)

[0092] Under ice-bath conditions, add thionyl chloride dropwise to anhydrous methanol, then add 5 g of compound 1, stir at room temperature for 5 h, thin-layer chromatography (TLG) monitors the completion of the reaction, evaporate the solvent to dryness, add ethyl acetate, and successively add water, Wash with saturated brine, dry over anhydrous sodium sulfate, and evaporate the solvent to dryness;

[0093] Wherein, the mass ratio of the product obtained in the third step to anhydrous methanol, thionyl chloride and ethyl acetate is 1:39.5:2:180, respectively.

[0094] The resulting product yield is 90.2%, 1 H NMR (CDCl 3 ): δ=0.86(t, 3H), 1.29(m, 2H), 1.72(m, 2H), 2.12(s, 3H), 3.68(s, 3H), 3.90(t, 2H), 6.78(s, 1H), 6.93 (d, J=8.8Hz, 1H), 7.82 (d, J=8.8Hz, 1H).

Embodiment 3

[0095] Example 3: Synthesis of 2-acetoxy-4-[2-(5-ethyl-2-pyridine)ethoxy]benzoic acid (compound 3)

[0096] Step 1: Suspend 5 g of 2,4-dihydroxybenzoic acid in a mixture of acetic anhydride and acetic acid, add mixed acid [98% sulfuric acid: 37% hydrochloric acid=1:1] (V:V), seal and heat up Reaction at 95°C for 1.5h, hot suction filtration, the filtrate was cooled in an ice bath to precipitate solids, filtered, and the filter residue was dried under reduced pressure at 65°C;

[0097] Add anhydrous potassium carbonate and dry N,N-dimethylformamide to the above filter residue, add benzyl bromide dropwise, react at room temperature for 3 hours, filter, add ethyl acetate to the filtrate, wash with water and saturated saline in sequence, and wash the organic layer with Dry over sodium sulfate, use petroleum ether: ethyl acetate = 3:1 (V:V) as eluent, separate by silica gel column chromatography and evaporate to dryness to obtain intermediate (II);

[0098] Wherein, the mass ratio...

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Abstract

The invention provides salicylic acid compounds with a structure shown as the following formula (I). In the formula (I), R1 refers to substituted alkyl having 1 to 6 carbon atoms, substituted aryl alkyl, or substituted aromatic heterocyclic alkyl; R2 refers to ethyl or acetyl; and R3 refers to hydrogen atom or methyl. The invention also provides two preparation methods for the salicylic acid compounds with the structure of the formula (I). The salicylic acid compounds have insulin-sensitizing activity.

Description

technical field [0001] The invention relates to a salicylic acid compound with insulin-sensitizing activity and a preparation method thereof, and belongs to the fields of medicinal chemistry and type 2 diabetes therapeutics. Background technique [0002] Diabetes mellitus is a metabolic disease that causes hyperglycemia due to absolute or relative insufficiency of insulin secretion in the body. Long-term hyperglycemia can lead to a series of chronic complications based on vascular lesions, leading to disability or death of patients, and seriously endangering human health. It has become the third major disease after cardiovascular and cerebrovascular diseases and malignant tumors. The World Health Organization (WHO) research shows that since the eighties of the 20th century, the number of diabetic patients has increased year by year with an average growth rate of about 10%. In 2000, the total number of diabetic patients in the world was 171 million (2.85%). According to WHO ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/16C07D213/55C07D263/32C07D209/18A61K31/215A61K31/44A61K31/421A61K31/404A61P3/10
Inventor 汤磊王建塔朱高峰
Owner 上海慈瑞医药科技股份有限公司
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